Stephen Sondheim and the Great Yom Kippur Morality Play

Socrates said: “The unexamined life is not worth living.” Judaism considers all lives worth living, but it considers the imperative to examine your life so important that every year it devotes ten days – from Rosh Hashanah until Yom Kippur – to the process of introspection and recalibrating your life.

An old Broadway show is the best illustration I know of the perils of the unexamined life. “Merrily We Roll Along,” with songs by the genius Stephen Sondheim, is the story of Frank Shepard, a nice guy and talented composer turned successful Hollywood producer. During a party in the opening scene, Frank is abandoned by his second wife, his “lifelong” friend, and his mistress. He cries out, “I hate my life!” This is the end of the story. The show works its way back in time, scene by scene, answering the refrain from the opening song, “How did you get there from here, Mr. Shepard? … How did you get to be you?”

“How did you get there from here, Mr. Shepard? … How did you get to be you?”

Gradually, the audience sees how Frank abandoned his youthful ideals and dreams, along with his first wife, his only child, and his two “lifelong” friends, through his heedless choices to pursue fame and fortune. The song, “Merrily We Roll Along,” paints a picture of the unexamined life, where the protagonist simply rolls along, unaware of where his choices are taking him. The lyrics could be a theme song for the Ten Days of Repentance that we are now in:

How does it happen?...
How did you get so far off the track?
Why don’t you turn around and go back?...
How did you ever get there from here?...
How does it slip away slow
So you never even notice it’s happening?...
How did you get there from here, Mr. Shepard?...
How did you get to be you?

Had Stephen Sondheim ever studied Maimonides’ tract on teshuva (repentance), he would have known that it’s always possible to “turn around and go back.” In fact, that’s the definition of teshuva. During this period leading up to Yom Kippur, every Jew is enjoined to “turn around” by examining his or her life. Take some time before Yom Kippur and ask yourself the hard questions, “Am I where and who I want to be? How did I get here? What choices did I make that landed me here?”

For example:

Did I want to be single at this age? What choices did I make that landed me here?

Do I want to have daily friction with my spouse? What choices do I routinely make that bring me to where I don’t want to be?

Do I want to be feuding with my sibling/s? What choices did I make that left me estranged from them?

What happened to my dream of being a patient, loving, parent? How did I become a yelling, critical parent instead?

Is this where I want to be in my career? Did I make bad choices to take the easy route or abandon my dreams out of fear of leaving my comfort zone?

Such self-assessment leads to the first step in the teshuva process: admitting you made a mistake. Usually, we are so invested in self-justification that we rationalize our bad choices. As the joke goes: What are the three words that every wife longs to hear from her husband? “I was wrong.” How sad that most of us value being right over being loved.

No one ends up where he/she doesn’t want to be without having made some bad choices along the way. Introspection identifies those bad choices. Going deeper ferrets out our motive for choosing the way we did. Was it fear? Was it desire? Was it arrogance? Was it laziness?

“I kept saying, ‘yes,’ when I really meant, ‘no.’”

Most of Frank Shepard’s bad choices were rooted in rank desire for wealth and physical pleasure, as well as spinelessness. Thus, in one scene, when his two old friends need him and are waiting for him, he succumbs to the seduction of a Broadway starlet and goes with her instead. As he says at the end, “I kept saying, ‘yes,’ when I really meant, ‘no.’”

Healthy Regret

The next step in the teshuva process is regret. Regret means regretting your own choices, not bemoaning your fate, as if you landed up here through no fault of your own. For a married person, this means not regretting that your spouse has certain bad qualities, but rather regretting that you fail to appreciate his/her good qualities. For a single person this may mean not bemoaning that there are no good men/women out there, but rather regretting that you rejected certain possible mates for spurious reasons.

Regret, as recommended by the 18th century sage Rabbi Shneur Zalman of Liadi, requires setting aside a defined time and plunging to the depths of sorrow for your bad choice. Such regret differs from guilt. Guilt is like a low-grade fever; you walk around with it, don’t deal with it, and it drags on and on. Regret, on the other hand, is like a high fever; you go to bed or take medication or see a doctor. When it’s over, it’s over.

During the time you have set aside to do teshuvah before Yom Kippur, set your timer for a few minutes and plunge to the depth of regret for what you have done. When the timer goes off, it’s over. The Talmud says that someone who repents and then revisits his sin is like a dog that vomits and goes back and eats its vomit. “Jewish guilt” is not Jewish. Instead, constructively use your pain to motivate you to change in a positive direction.

A Jew practices “regret” not by feeling like a lowly sinner, but rather by asserting one’s inherent greatness and how the wrong act betrayed that. The three minutes of regret should sound like: “How could someone like me do something like that? How could someone who had such ideals have stooped to act like that? How could someone with my knowledge and values have acted so wrongly?”

Plan for the Future

The next step of teshuva is to make a plan for the future to act differently. How did you get so far off the track? Why don’t you turn around and go back? A Jew can always turn around and go back. The plan must be concrete and comprised of small steps rather than grandiose resolutions that are doomed to fail.

You’re critical of your spouse or children? Dedicate one hour a day to a “criticism fast” where, no matter what, you won’t indulge your critical nature. You gossip? Undertake one hour a day when no negative words about other people will cross your lips. You don’t call your mother because she pushes your buttons? Undertake to call her once a week for ten minutes (and gradually increase that to twice a week).

Ask Forgiveness

If your wrong choices have hurt other people, there’s a fourth step: Ask forgiveness. The relative or friend you’re feuding with? Forget the autopsy of the original argument and who is wrong; just call him or her and say, “I really miss our relationship. I’m sorry for my part in distancing you. Please forgive me and let’s be friends.”

Step five pertains only when property is involved. If you stole something, whether it was from a store or a neighbor, you must return it. This includes borrowing an item and forgetting to give it back. Make sure that there’s nothing in your home that you didn’t come by honestly by purchasing it or receiving it as a gift.

“Merrily We Roll Along” flopped on Broadway in 1981. Based on a 1934 play by George S. Kaufman and Moss Hart (both Jews), the story is a modern morality play, warning against the perils of failing to regularly examine one’s choices and recalibrate one’s life. The last scene, which takes place 19 years before the first cataclysmic party scene, shows the three young friends fired up with enthusiasm to change the world. Of course the audience left the theater disgusted that Frank betrayed both his ideals and those who loved him. If only Frank had realized that he could still change not the world, but himself! The show would have been better if Maimonides had written the final act.

Sara Yoheved Rigler is a popular international lecturer on subjects of Jewish spirituality. She has given lectures and workshops in Israel, England, France, South Africa, Mexico, Canada, Chile, Panama, and over 35 American cities. She is one of the most popular authors on Aish.com, world’s biggest Judaism website, and is a columnist for Ami Magazine. Sara Yoheved Rigler is the author of five best-sellers: Holy Woman; Lights from Jerusalem; Battle Plans: How to Fight the Yetzer Hara (with Rebbetzin Tziporah Heller); G-d Winked; and Heavenprints . She gives a weekly Marriage Webinar for Jewish Workshops on a spiritual approach to marriage, with hundreds of members throughout the world. She lives in the Old City of Jerusalem. Her newest book, Emunah with Love and Chicken Soup, the story of Henny Machlis, the Brooklyn-born girl who became a Jerusalem legend, was was released in November, 2016. Her website is: sararigler.com.

Examining ones life is something smart people from all cultures have always done . Normally you have to be older and have some history in order to accumulate some regrets . Youth can make mistakes and recover however it's those of us who have most of our life behind us whos bad decisions have greater meaning . I remember a Talking Heads song " Once in a Life Time" that tackled this subject in a humorous way . Having regrets is normal and unavoidable . People make wrong decisions and wind up in wonderful places while others are thoughtful and wind up in the bowels of hell . There is no one way to navigate through life and no particular way to know if there is a purpose . Peace and perfection does not create any movement in any direction . It is the collislon between people , planets and the universe that creates a new direction and new life . You let your instincts guide you through this life and then accept death gracefully